IL197777A - Enantiomerically pure phosphoindoles as HIV inhibitors - Google Patents

Info

Publication number

IL197777A

IL197777A IL197777A IL19777709A IL197777A IL 197777 A IL197777 A IL 197777A IL 197777 A IL197777 A IL 197777A IL 19777709 A IL19777709 A IL 19777709A IL 197777 A IL197777 A IL 197777A

Authority

IL

Israel

Prior art keywords

compound

hiv

acid

pharmaceutical composition

nmr

Prior art date

2006-09-29

Links

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• 239000003112 inhibitor Substances 0.000 title claims description 33
• 150000003006 phosphoindoles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 336
• -1 hydrate Chemical class 0.000 claims description 174
• 238000000034 method Methods 0.000 claims description 124
• 239000000203 mixture Substances 0.000 claims description 111
• 150000003839 salts Chemical class 0.000 claims description 97
• 229910052739 hydrogen Inorganic materials 0.000 claims description 94
• 239000001257 hydrogen Substances 0.000 claims description 88
• 238000011282 treatment Methods 0.000 claims description 73
• 239000003814 drug Substances 0.000 claims description 66
• 125000000217 alkyl group Chemical group 0.000 claims description 63
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 60
• 239000003795 chemical substances by application Substances 0.000 claims description 46
• 150000002148 esters Chemical class 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 28
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• 150000002367 halogens Chemical class 0.000 claims description 27
• 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 20
• 208000031886 HIV Infections Diseases 0.000 claims description 19
• 239000002259 anti human immunodeficiency virus agent Substances 0.000 claims description 18
• 208000037357 HIV infectious disease Diseases 0.000 claims description 17
• 125000003368 amide group Chemical group 0.000 claims description 17
• 229940124411 anti-hiv antiviral agent Drugs 0.000 claims description 17
• 239000003937 drug carrier Substances 0.000 claims description 17
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 17
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 16
• 208000015181 infectious disease Diseases 0.000 claims description 16
• QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 16
• CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims description 15
• 239000002777 nucleoside Substances 0.000 claims description 15
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical group C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims description 14
• 229960001852 saquinavir Drugs 0.000 claims description 14
• HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims description 14
• XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 claims description 13
• 125000005518 carboxamido group Chemical group 0.000 claims description 13
• 229960001936 indinavir Drugs 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims description 12
• 229960001830 amprenavir Drugs 0.000 claims description 12
• QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims description 12
• 229960000884 nelfinavir Drugs 0.000 claims description 12
• VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 claims description 12
• 108010019625 Atazanavir Sulfate Proteins 0.000 claims description 11
• 125000000539 amino acid group Chemical group 0.000 claims description 11
• 229940124524 integrase inhibitor Drugs 0.000 claims description 11
• 239000002850 integrase inhibitor Substances 0.000 claims description 11
• KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 claims description 10
• 125000002252 acyl group Chemical group 0.000 claims description 10
• AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 claims description 10
• WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims description 10
• AXRYRYVKAWYZBR-UHFFFAOYSA-N Atazanavir Natural products C=1C=C(C=2N=CC=CC=2)C=CC=1CN(NC(=O)C(NC(=O)OC)C(C)(C)C)CC(O)C(NC(=O)C(NC(=O)OC)C(C)(C)C)CC1=CC=CC=C1 AXRYRYVKAWYZBR-UHFFFAOYSA-N 0.000 claims description 9
• 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 9
• 229960003277 atazanavir Drugs 0.000 claims description 9
• CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims description 9
• MLBVMOWEQCZNCC-OEMFJLHTSA-N fosamprenavir Chemical compound C([C@@H]([C@H](OP(O)(O)=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 MLBVMOWEQCZNCC-OEMFJLHTSA-N 0.000 claims description 9
• 229960003142 fosamprenavir Drugs 0.000 claims description 9
• JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 9
• 150000003833 nucleoside derivatives Chemical class 0.000 claims description 9
• 108010092853 peginterferon alfa-2a Proteins 0.000 claims description 9
• 230000010076 replication Effects 0.000 claims description 9
• SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• SUJUHGSWHZTSEU-UHFFFAOYSA-N Tipranavir Natural products C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 SUJUHGSWHZTSEU-UHFFFAOYSA-N 0.000 claims description 8
• RLAHNGKRJJEIJL-RFZPGFLSSA-N [(2r,4r)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1CO[C@@H](CO)O1 RLAHNGKRJJEIJL-RFZPGFLSSA-N 0.000 claims description 8
• 239000002775 capsule Substances 0.000 claims description 8
• 229960005107 darunavir Drugs 0.000 claims description 8
• JUZYLCPPVHEVSV-LJQANCHMSA-N elvitegravir Chemical compound COC1=CC=2N([C@H](CO)C(C)C)C=C(C(O)=O)C(=O)C=2C=C1CC1=CC=CC(Cl)=C1F JUZYLCPPVHEVSV-LJQANCHMSA-N 0.000 claims description 8
• 229960001627 lamivudine Drugs 0.000 claims description 8
• 229960004525 lopinavir Drugs 0.000 claims description 8
• NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 8
• 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 8
• 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 claims description 8
• 229960004742 raltegravir Drugs 0.000 claims description 8
• CZFFBEXEKNGXKS-UHFFFAOYSA-N raltegravir Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C CZFFBEXEKNGXKS-UHFFFAOYSA-N 0.000 claims description 8
• 229960000838 tipranavir Drugs 0.000 claims description 8
• 229960002555 zidovudine Drugs 0.000 claims description 8
• BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims description 7
• 229960004748 abacavir Drugs 0.000 claims description 7
• MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 7
• XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 claims description 6
• WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims description 6
• FCLYPCIMVVLLRN-FXSYQQGGSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,3r)-1-[4-(diethoxyphosphorylmethoxy)phenyl]-3-hydroxy-4-[(4-methoxyphenyl)sulfonyl-(2-methylpropyl)amino]butan-2-yl]carbamate Chemical compound C1=CC(OCP(=O)(OCC)OCC)=CC=C1C[C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(OC)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1 FCLYPCIMVVLLRN-FXSYQQGGSA-N 0.000 claims description 6
• 229950005846 amdoxovir Drugs 0.000 claims description 6
• 229960002656 didanosine Drugs 0.000 claims description 6
• XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims description 6
• 229960003586 elvitegravir Drugs 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 229960004556 tenofovir Drugs 0.000 claims description 6
• 229960000523 zalcitabine Drugs 0.000 claims description 6
• QWLNINWUBHHOLU-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-4-hydroxy-n-(2-hydroxyethyl)-1-methyl-2-oxo-1,5-naphthyridine-3-carboxamide Chemical compound C=1N=C2C(O)=C(C(=O)NCCO)C(=O)N(C)C2=CC=1CC1=CC=C(F)C=C1 QWLNINWUBHHOLU-UHFFFAOYSA-N 0.000 claims description 5
• XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 claims description 5
• 108010032976 Enfuvirtide Proteins 0.000 claims description 5
• GLWHPRRGGYLLRV-XLPZGREQSA-N [[(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](N=[N+]=[N-])C1 GLWHPRRGGYLLRV-XLPZGREQSA-N 0.000 claims description 5
• WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims description 5
• GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 claims description 5
• 229940014461 combivir Drugs 0.000 claims description 5
• 229960003804 efavirenz Drugs 0.000 claims description 5
• 229960000366 emtricitabine Drugs 0.000 claims description 5
• PEASPLKKXBYDKL-FXEVSJAOSA-N enfuvirtide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 PEASPLKKXBYDKL-FXEVSJAOSA-N 0.000 claims description 5
• 229960002062 enfuvirtide Drugs 0.000 claims description 5
• IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 claims description 5
• 229940111527 trizivir Drugs 0.000 claims description 5
• 229940008349 truvada Drugs 0.000 claims description 5
• CNPVJJQCETWNEU-CYFREDJKSA-N (4,6-dimethyl-5-pyrimidinyl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl]methanone Chemical compound N([C@@H](COC)C=1C=CC(=CC=1)C(F)(F)F)([C@H](C1)C)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)N=CN=C1C CNPVJJQCETWNEU-CYFREDJKSA-N 0.000 claims description 4
• GWNHAOBXDGOXRR-HJFSHJIFSA-N 9-[2-[[(2r,4s)-4-(3-chlorophenyl)-2-oxo-1,3,2$l^{5}-dioxaphosphinan-2-yl]methoxy]ethyl]purin-6-amine Chemical compound C1([C@@H]2CCO[P@](O2)(=O)COCCN2C=3N=CN=C(C=3N=C2)N)=CC=CC(Cl)=C1 GWNHAOBXDGOXRR-HJFSHJIFSA-N 0.000 claims description 4
• 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 4
• 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 4
• YJEJKUQEXFSVCJ-WRFMNRASSA-N bevirimat Chemical compound C1C[C@H](OC(=O)CC(C)(C)C(O)=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C YJEJKUQEXFSVCJ-WRFMNRASSA-N 0.000 claims description 4
• 229960005338 clevudine Drugs 0.000 claims description 4
• 229960005319 delavirdine Drugs 0.000 claims description 4
• GSNHKUDZZFZSJB-QYOOZWMWSA-N maraviroc Chemical compound CC(C)C1=NN=C(C)N1[C@@H]1C[C@H](N2CC[C@H](NC(=O)C3CCC(F)(F)CC3)C=3C=CC=CC=3)CC[C@H]2C1 GSNHKUDZZFZSJB-QYOOZWMWSA-N 0.000 claims description 4
• 229960004710 maraviroc Drugs 0.000 claims description 4
• 230000035800 maturation Effects 0.000 claims description 4
• 230000007935 neutral effect Effects 0.000 claims description 4
• 229960001203 stavudine Drugs 0.000 claims description 4
• 208000024891 symptom Diseases 0.000 claims description 4
• 229960005311 telbivudine Drugs 0.000 claims description 4
• 229950009860 vicriviroc Drugs 0.000 claims description 4
• NIDRYBLTWYFCFV-FMTVUPSXSA-N (+)-calanolide A Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-FMTVUPSXSA-N 0.000 claims description 3
• GWNOTCOIYUNTQP-FQLXRVMXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 GWNOTCOIYUNTQP-FQLXRVMXSA-N 0.000 claims description 3
• HSBKFSPNDWWPSL-VDTYLAMSSA-N 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1C=C[C@H](CO)O1 HSBKFSPNDWWPSL-VDTYLAMSSA-N 0.000 claims description 3
• 102100039864 ATPase family AAA domain-containing protein 2 Human genes 0.000 claims description 3
• NIDRYBLTWYFCFV-IUUKEHGRSA-N Calanolide A Natural products C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-IUUKEHGRSA-N 0.000 claims description 3
• 101000887284 Homo sapiens ATPase family AAA domain-containing protein 2 Proteins 0.000 claims description 3
• 108010078049 Interferon alpha-2 Proteins 0.000 claims description 3
• 229940123527 Nucleotide reverse transcriptase inhibitor Drugs 0.000 claims description 3
• VFCYZPOEGWLYRM-QCZKYFFMSA-N [(2s,3r,5s)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] (2s)-2-amino-3-methylbutanoate Chemical compound O1[C@@H](CO)[C@H](OC(=O)[C@@H](N)C(C)C)C[C@H]1N1C(=O)N=C(N)C=C1 VFCYZPOEGWLYRM-QCZKYFFMSA-N 0.000 claims description 3
• JLKJXDOWBVVABZ-UHFFFAOYSA-N [[1-[(2-aminopurin-9-yl)methyl]cyclopropyl]oxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate Chemical compound C1=NC2=CN=C(N)N=C2N1CC1(OCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)CC1 JLKJXDOWBVVABZ-UHFFFAOYSA-N 0.000 claims description 3
• 229960003205 adefovir dipivoxil Drugs 0.000 claims description 3
• 229950006356 aplaviroc Drugs 0.000 claims description 3
• RYMCFYKJDVMSIR-RNFRBKRXSA-N apricitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1S[C@H](CO)OC1 RYMCFYKJDVMSIR-RNFRBKRXSA-N 0.000 claims description 3
• 229950007936 apricitabine Drugs 0.000 claims description 3
• 229940068561 atripla Drugs 0.000 claims description 3
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